


Quickies

by Nepenthene



Category: Supernatural
Genre: Accidental Cuddling, Alternate Universe, Castiel and Dean Winchester Have a Profound Bond, Crowley is a delightful Scottish asshole, Dean Winchester Has a Fear of Flying, Dean and Crowley had a thing, Dean is about as smooth as sandpaper, Dreams, Flustered Dean Winchester, Gen, Graduate Student Castiel (Supernatural), Hurt/Comfort, Inspired by Music, M/M, Mechanic Dean Winchester, Nightmares, One Shot Collection, Sam ships Destiel, Season/Series 05, Shitty Motel Pools, Shrinking Spells, Smooth Castiel (Supernatural), Smug Castiel (Supernatural), and Dean REALLY doesn’t want Sam to know, the boys are goofballs
Language: English
Status: In-Progress
Published: 2020-09-11
Updated: 2021-01-05
Packaged: 2021-03-06 16:00:21
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 6
Words: 5,676
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26411521
Author URL: https://archiveofourown.org/users/Nepenthene/pseuds/Nepenthene
Summary: Oneshot dumping ground!1. We’re on a plane and you hate flying2. Nightmare hurt/comfort3. Shitty motel pool time4. Tiny Cas5. Crowley comes to visit6. “Cherry Pie” gives Dean ~*ideas*~Come say hi and give me some requests!
Relationships: Castiel & Dean Winchester & Sam Winchester, Castiel/Dean Winchester, Dean Winchester & Sam Winchester, past Crowley/Dean Winchester - Relationship
Comments: 24
Kudos: 56





	1. Fear of Flying

**Notes for the Chapter:**

> "This is a five hour long plane ride, we're sitting together and you're deathly afraid of flying" AU

_11:46 AM, Sioux Falls International Airport_

Castiel trudges down the aisle of the airplane, his carry-on catching on every few seats and threatening to clothesline him with the cross-body strap. He’s hot and flustered from his sprint across the airport, and each jolt of resistance feels like a personally engineered torment to obliterate his already frayed nerves. 

But despite everything that happened this morning, he made his flight on time. And, he thinks with a relieved sigh as he shoves his bag into the overhead and collapses into his seat, from here on out there’s not much that can go wrong. For the next week, he’s free: from his thesis, from being a good TA, from everything. Gabriel is no doubt planning for a week of debauchery and hedonism, but Castiel has every intention of going to bed at a reasonable hour every night, taking the time for a nice, long run every morning, and spending the rest of the days doing whatever the hell he wants. 

He takes off his trench coat and folds it up neatly, wedging it behind his head and pulling the safety brochure out of the mesh pocket on the seat in front of him. At least it seems like this will be a calm flight. He didn’t see any young children when he came aboard, and it’s a sunny, clear day. And even better, there doesn’t seem to be anyone sitting beside him. 

“You’re in my seat.”

Castiel blinks up at the man standing in the aisle, startled, and frowns. “Are you sure?” He fishes his ticket out of his pocket and stifles a sigh when he sees that yes, he is in the wrong seat. His cursory glance on the way in must not have been long enough. “Yes, it appears I am.”

He moves to get up, still awkwardly holding the safety booklet, but the man stops him with a wave of his hand. “Nah, it’s fine, I don’t like the window seat anyways. I’ll just take the aisle.”

Castiel shoves his ticket back into his pocket and stops, slightly stunned, as he gets his first real look at the man. 

Because, fuck. He’s _extremely_ attractive. He looks to be around Castiel’s age, with a face straight out of classical sculpture and an endearing smattering of freckles across the tanned planes of his cheeks. His green eyes have smile crinkles at the corners, and his mouth is a near-perfect cupid’s bow tipped into a crooked half-smile. 

He’s also holding a hand out in Castiel’s direction. Castiel’s brain kicks back into gear and he hastily shakes it, though he’s definitely already come off as strange if the man’s bemused expression is anything to go by. 

“I’m Dean.”

“Castiel. Again, my apologies about the mistake.”

Dean raises an amused eyebrow. “No problem. Like I said, I’m not attached to the window seat. Have at it, man.”

Castiel chances a small smile and pulls his phone out of his pocket, pulling up the book he’d started yesterday while he curses his social ineptitude. Normally he likes to think he’s not quite _this_ bad, but today is simply awful. 

The man, Dean, doesn’t try to continue the conversation, though, so Castiel doesn’t have to suffer any more than he already is. A few announcements come over the intercom as the plane prepares to taxi, and Castiel finally starts to relax. It’s a five-hour flight, yes, but he’s always enjoyed flying. He feels almost at home whenever he’s up above the clouds. 

At some point, Dean starts humming. Castiel doesn’t recognize the tune, but he picks up on an urgent undercurrent in Dean’s voice that he doubts is part of the song. He glances down at the armrests, and his suspicions are confirmed: Dean’s holding onto the sticky plastic for dear life. As the plane gives a lurch and starts to taxi down the runway, the humming hitches and Dean’s hands squeeze the armrests even tighter, his knuckles showing white through his skin.

“Would you like a piece of gum?”

Dean looks at Castiel, eyes wide. “Uh. What?”

Castiel shrugs. “To help you adjust to the pressure. It keeps your ears from popping.”

Dean takes a piece from the pack with jittery fingers, grumbling, “Wouldn’t have to worry about my goddamn ears popping if I was passed out, but I forgot my Xanax at home.” He pops the piece of gum into his mouth, then stops mid-chew and shoots Castiel an awkward glance. “Uh, I mean…”

Castiel attempts to keep a straight face, but a smile slips out. “Unfortunately, I don’t have any of that in my pockets.”

Dean seems relieved that Castiel doesn’t think he’s some sort of addict, and lets out a brief huff of laughter. “Well shit, that’s my backup plan out the window.” The airplane starts picking up speed, and Dean plasters himself to the seat, his eyes squeezed shut and his hands back to strangling the armrests. “Fuck,” he wheezes. “So what are you doin’ in California, Castiel?”

“I’m visiting my brother for a week.”

Dean’s so surprised, he looks like he almost forgets he’s having a minor crisis. “Shit, really? Me too. Older or younger?”

Castiel tries not to make a face. “Older. Technically.”

Dean laughs a little. “Oh yeah, you get it. My little brother just passed his bar exam out there, so we’re celebrating.”

“Congratulations. I’m sure you’re very proud.”

“Thanks, dude. I really am, _oh shit-”_

Dean spends the ascent swearing a blue streak under his breath, beginning with an incoherent litany of random curses and graduating to personal insults directed at the pilot, the taxi driver that brought him to the airport, someone named Sam, and God, just to name a few. Castiel listens in a kind of awe, and thinks even Gabriel would be impressed with Dean’s creativity.

Finally, the seatbelt light clicks off with a soft _ding_ and a steward announces they’ve reached cruising altitude over the intercom. Dean lets out a shaky breath and looks over at Castiel. “Your, uh. Your brother sounds like a real character, huh?”

Castiel recognizes the silent plea for further distraction for what it is, and obliges with an exasperated grin. “You have no idea. He insisted on organizing my twenty-first birthday party, and he ended up incurring four thousand dollars in property damages…”

_12:27 PM_

“See? _This_ is Baby. 1967 Chevy Impala, still runs as smooth as she did when she rolled off the line. Maybe even a little better.”

“Ah, yes. It’s very nice.”

Dean’s hand flies to his chest in mock affront. “Excuse you, Cas, _she_ is a _lady_. And fuck yeah, she’s nice.” Then he pauses, eyeing Castiel shrewdly. “You don’t know the first thing about cars, do you?”

“I admit that I am lacking in that area of expertise. But you obviously love your vehicle very much, and she looks extremely well taken care of.”

“You bet your ass she is. I wish I could take you for a spin, you’d love it.”

_2:38 PM_

“... seriously? Nothing? How do you not know Star Wars?”

“My parents were very strictly religious. They didn’t approve of most popular culture, so unfortunately, Star Wars fell by the wayside.”

“Shit, dude, you’ve gotta watch it. It is a _classic_ . Just make sure you start with _A New Hope_ and not _Phantom Menace._ ”

“Why? What’s wrong with _Phantom Menace_?”

“Oh man, don’t even get me _started_ …”

_3:59 PM_

“… Michael and Lucifer have been fighting since we were children, and even though I’ve told them in no uncertain terms I will not be getting in the middle of their corporate pissing match, they’re still both trying to recruit me.”

“Wait… your brother’s name is Lucifer? Like, Satan? Are you fucking with me, or...?”

“Unfortunately, I am not ‘fucking’ with you. His _legal_ name is Nick, but he’s been calling himself Lucifer ever since our father kicked him out. It’s just easier to go along with it.”

“Uh… wow.”

“Yes. You could say he has a few issues.”

“Hey, I get it. Really. Sammy an’ I are both fucked six ways to Sunday after how we grew up. The only difference is that he deals with it a helluva lot better than I do...”

_5:21 PM, LAX_

“Welcome to Los Angeles International Airport. We hope you enjoy your stay here in lovely California!”

Dean lets out a huge sigh of relief. “Yeah, yeah. Eat me, lady.”

Castiel huffs a laugh, and Dean grins back. They’re both still pleasantly buzzed from the two in-flight whiskies they had, but Castiel can tell that Dean really is anxious to get off the plane. He tries not to let his growing disappointment show on his face as they get up and start shuffling down the aisle; as silly as it is, he thinks he’ll miss Dean. Although honestly, he says to himself, who wouldn’t?

Dean keeps chatting as they make their way off the plane, and laughs out loud when Castiel glowers at a woman who pushes past them with her husband. (“You looked like you were gonna smite her or something, dude,” he’d laughed. “Like you were gonna get Biblical on her ass.”)

They pick up their bags at the carousel, and suddenly they’ve reached the moment Castiel knew was coming. He puts on a pleasant expression and nods solemnly at the other man. “I believe this is where we part ways. It was very nice to meet you, Dean. Congratulations again to your brother.”

Dean shakes his outstretched hand, an odd expression on his face. “Yeah, Cas. You’re a good guy. Thanks for putting up with my bullshit that whole time, you didn’t have to do that.”

Castiel shakes his head. “It was no trouble, I assure you. You are… easy to talk to.” 

Dean smiles softly. “Thanks.” Both of them pause, neither willing to be the first to leave. Castiel’s heart gives a treacherous thump. Maybe…

No. Gabriel’s probably waiting for him, anyways. He steps back, waving awkwardly. “Well, enjoy your trip. Goodbye, Dean,” he says, and turns determinedly towards the Arrivals gate.

“Wait.” A hand closes over Castiel’s shoulder, and he stops. He turns back to Dean, head tilted in confusion. 

“Yes?” 

Dean flushes slightly and pulls his hand back, running it through his hair. “Uh, could I actually… could I get your number? I’d like to see you again if I make it back to Sioux Falls alive.”

Castiel tries not to gape. “Uh. See me again?”

“Yeah, like, uh. On a date. If you’d be into that.”

Castiel feels a smile growing on his face. “Yes, Dean. I would be into that. Very much.”

Dean beams, his chest puffing out a little. “Awesome.” He hands over his phone, and Castiel scrolls thoughtfully through the emoji keyboard before sending a little plane emoji to his number. Dean snorts when he sees it, shaking his head. “I guess I’ll see you ‘round, Cas.”

Castiel grins. “Oh, yes. I’m certain of it.”

**Notes for the Chapter:**

> This is from a list of "meet-ugly" prompts put together by tokiosunset on tumblr. Unfortunately I can't find their tumblr anywhere, but it's a fun list of prompts nonetheless.
> 
> And hey, let's play some trivia: what's the song that Dean likes to hum to keep himself calm? Put your guess in the comments. :)
> 
> (P.S. Constructive criticism welcome.)


	2. My Brother's Keeper

**Summary for the Chapter:**

> "Sam has never told Dean this, but during some of his nightmares Sam will wake up and Cas will be sitting at the foot of Dean’s bed whispering things in Enochian until Dean stops shaking in his sleep."

It’s the fuzzy grey of _very_ early morning in the motel room, and Sam can’t figure out why he’s in any state to be aware of that. He squints at the blurry red numbers on the old alarm clock and rubs a hand over his face, blearily trying to figure out what the hell woke him up.

Barely a second later, he gets it. A soft whimper and an agitated rustle of sheets reach his ears from across the room, and Sam sighs quietly. Dean must be having another nightmare. He grimaces in sympathy but stays where he is: he’s awake enough now not to do something stupid, like try and help. Last time he did _that_ he got a black eye for his trouble, which of course made Dean feel even worse than he already did when he actually woke up. So Sam just lies there in the dark, listening to Dean’s choked-off sobs, and tries not to feel like the worst brother ever. 

But then suddenly Dean is shouting something incomprehensible, his voice ragged and broken. Sam doesn’t catch most of it as he bolts upright and struggles to untangle his legs from the sheets, but the final cry is distinct and achingly desperate:

“CAS!”

_Whoosh._

Sam freezes, halfway out of bed, and stares across the room with his mouth hanging open. 

A shadowy figure with familiar messy hair and a long coat is standing next to Dean’s bed, leaning over him protectively and placing it’s hand firmly on Dean’s shoulder. The same one the handprint was on, Sam remembers absently as he swallows back the shout of warning that’s stuck in his throat.

Cas starts speaking gently to Dean in that strange, melodic language of his, a low, indistinct murmur filling the room. And to Sam’s shock, Dean starts to relax.

What the fuck. How is this happening? Sam was _lucky_ all he got was a punch in the face.

Despite the dimness of the room, Sam can actually _see_ the tension bleeding from Dean’s limbs, his hands gradually releasing their _rigor mortis_ grip on the rumpled sheets. His big brother curls towards Cas, his breathing becoming natural and even again, and Cas slowly lets the comforting rumble of his voice fade back to silence. 

Dean settles further into his pillow, a contented sigh whispering through the air. Cas pauses for a minute, watching Dean intently. Whatever he sees must satisfy him, because he silently removes his hand and gently tugs the covers a little further up over Dean's chest. 

Sam blinks a couple times and closes his mouth, suddenly uncomfortable. He wasn't meant to see this. Maybe if he just...

The bed creaks loudly as he shifts, and he goes still as Cas’ head snaps up. Sam grits his teeth, cursing the shitty bedsprings as he and Cas stare at each other, saying nothing. Dean starts snoring softly.

Cas nods once, almost apprehensively. Sam manages a small wave in return.

Then he’s gone, just as abruptly as he'd appeared. 

It's a long time before Sam manages to fall back asleep.

  
...

When he's woken up the next morning by a passionate rendition of “Thunderstruck” emanating from the shower, Sam's first instinct is to tell Dean what happened. 

But for some reason, he doesn’t.

He only makes a face and swats Dean’s hand away when Dean ruffles his hair and calls him “Sleeping Beauty”, ignoring the words crowding up behind his lips. And then over breakfast at a nearby Denny’s, when Dean asks if he slept all right, because, “Dude. You look like shit,” he just rolls his eyes, calls him a jerk, and goes back to eating his pancakes.

Because really, Sam reasons as they’re driving out of town, it’s not any of his business. And if he starts to notice now how much better Dean’s been sleeping lately, or how Dean will occasionally complain exasperatedly about waking up with a certain angel watching over him, well. What does Sam know about that?

(He knows that Cas’ll be there when Dean needs him. And that’s enough for him.)

**Notes for the Chapter:**

> This was from a screenshot of a tumblr post I came across on Instagram, no username included. It just gave me so many feels, and I had to write it because Cas has t o t a l l y done this. You can't tell me otherwise. ;D
> 
> Don't be afraid to drop a comment and say hi!


	3. Shitty Motel Pools Aren't That Bad

**Notes for the Chapter:**

> “it’s been brought to my attention that we’ve never seen the boys hanging out in a shitty motel pool”

Sam looks up from his phone, confused, as Dean pulls into a parking spot and kills the engine. “What’s up?”

Dean doesn’t say anything, just looks past Sam out of the passenger window with his thinking face on. Sam looks too, but the only thing that’s out there is one of those general stores that every small town seems to have, the ones that sell everything from toy bucket and shovel sets to gardening tools to bird feeders. 

Dean just grins. “C’mon.”

Sam groans, but he gets out of the car anyways. “Dude, can we just go back to the motel? I want to take a shower. And you’ve been complaining about how hot you are  _ all day.” _

A little bell rings as they walk through the door, and Dean makes a beeline for a rack of cheap swim trunks, rifling through eye-aching Hawaiian prints, stripes, and… is that Homer Simpson? He finds a really awful pair with boats and azalea flowers, and holds them up. “Whaddya think? Do they match my eyes?”

Sam… Sam is so confused. “What?”

Dean rolls his eyes, snagging the Simpsons ones too before making for the cash. “You just said it. It’s hot as balls, these monkey suits’ve been driving me crazy all day, and I just remembered that the motel’s got a pool. Plus, I doubt the management’d be too pleased if we went skinny-dipping, so swim trunks it is.”

Sam snorts a little in disbelief. “You… you want to go swimming?”

Dean grins, tossing the trunks onto the counter and digging out his wallet. “Yep. And you’re gonna come with me.”

— - —

Sam tosses the mini bottle of sunscreen at Dean, and it bounces off his shoulder with a plasticky  _ thwack. _ Dean narrows his eyes. “Hey. Knock it off.”

Sam laughs. “Just covering my bases. You can’t tell me I didn’t warn you when you’ve got third degree sunburns tomorrow morning.”

Dean sighs long-sufferingly and picks up the bottle, haphazardly smearing some sunscreen over his arms, his shoulders, and his face. Sam suppresses a grin and wonders if he’ll be able to sneak a picture of the blob on Dean’s nose before he notices.

Even though he got stuck with the Simpsons trunks, Sam has a good time. The water’s actually fairly clean, and it’s a  _ huge _ relief after being stuck in their cheap polyester agent suits all day. He does a few laps, until Dean splashes him and tells him not to be lame. Which is an act of war, obviously, so Sam splashes him back and they get into a huge water fight that only ends when they’re both laughing too hard to keep going. Sam just knows he’s gonna be spitting the taste of chlorine out of his mouth for days.

He’s floating on his back, staring up at the sky, and it occurs to him that he doesn’t remember the last time they had this much fun. Maybe that day they canvassed the haunted arcade, and they were trying to destroy each other at pinball? That was… hm. That was too long ago. They should try and do this more often.

He looks over at Dean and grins. “Hey. This was a good idea.”

Dean looks proud of himself as he climbs up the ladder and walks toward the chair where he left his towel. “Of course it was. I’m awesome, remember?”

Sam laughs. “At losing water fights, maybe.”

Dean stops, turning back towards the pool with an evil glint in his eye. “Oh, really?”

Sam’s eyes go wide. “Wait, I was just kidding—”

He’s still yelling when Dean’s cannonball sends a wave crashing into him. And just like that, round two of the Great Winchester Water War is officially _on._

**Notes for the Chapter:**

> The original blog this came from seems to be deactivated, but [ here](https://lemondropsonice.tumblr.com/post/189366812803/wincestily-its-been-brought-to-my-attention-that) is a good quality repost. I've seen this on insta a few times, and it's just such a cute idea. 
> 
> Drop requests in the comments, I'd love some inspo!


	4. Shrunk in Love

**Summary for the Chapter:**

> Cas gets shrunken down to eight inches tall.

**Notes for the Chapter:**

> This chapter was based on [this](https://www.instagram.com/p/B0lg-qyo-Em/?utm_source=ig_web_copy_link) post on Instagram by reshipkmn. Their stuff is great, I love their style, and this was just so cute. You can check them out on here under the same name as well!

“Stop laughing, Dean. This isn’t funny,” Cas grumbles, crossing his arms and  _ glowering. _

“C’mon, man,” Dean snickers. “It’s kinda funny.”

Cas’ expression turns downright murderous, and Dean struggles not to laugh out loud. Because the angel’s normally intimidating death glare is missing the mark _ just _ a little, seeing as he’s currently eight inches tall.

It’s okay, he’s fine; they’d called Rowena in to take a look at him as soon as she could, and according to her diagnosis he’s just gonna have to wait this one out. They’d been on a hunt, and the leprechaun they’d been after had set a swarm of pixies on them. When Cas had gotten a bunch of them to the face he’d stumbled back in surprise,  right into a magical booby trap he’d just made his way around. The spell went off with a bang and a billowing cloud of blue smoke, and when it cleared Cas had been shrunken down to the size of a Ken doll. Sam and Dean had gotten the ugly Irish bastard, at least, and banished him back to the faerie realm with  _ extreme _ prejudice, but that still left them with one very small,  _ very _ pissed off angel of the Lord.

They’re having a bit of a hard time taking it seriously. 

The leprechaun had been hiding out in a second-floor apartment, so Cas’d had to suck it up and ride downstairs to the car in Dean’s breast pocket. That’d been weird, feeling the tiny, warm weight against his chest and knowing it was  _ Cas _ . And it was even weirder when he poked his head out once they were in the car, his hair looking even more like someone had just been running their hands through it than usual, so he could demand to sit on the seat.

That’d been short-lived: they’d stopped at the light at the end of the street, and Cas had gone flying straight into the footwell. He’d gotten into Sam’s pocket after that, though, because Dean was too busy laughing so hard he could barely breathe. 

But that was before Rowena didn’t have a fix; now Cas has been the size of a kid’s toy for roughly forty-eight hours, and he’s completely fed up with the state of things. He can’t drink coffee, it takes him forever to get anywhere, and reading or watching TV on his own have turned into nigh impossible tasks. He has to get help with  _ everything,  _ and it’s really grating on him. 

(For example: Sam had been poking at him with some kind of incense earlier, trying to test something or other, and Cas had threatened to stab him with his angel blade if he didn’t back off. Which, yeah, it’s roughly the size of a toothpick right now, but still. His fuse is pretty short.)

So it’s odd when he suddenly drops the death glare he’s leveling at Dean, letting out a dejected kind of sigh. His shoulders slump a little and he turns away, his hands clenched at his sides. Dean immediately sobers up, because he might be an asshole, but he’s not a  _ complete  _ dickwad.

He leans forward, resting his arms on the table. “Hey. You okay?”

Cas doesn’t look at him. “Yes. Thank you for asking, Dean.”

Dean raises an eyebrow. “Oh yeah, that was  _ real _ convincing.” Cas shoots him a disgusted look, and Dean shrugs. “Seriously, what’s eating you? Are you just weirded out by this whole thing?”

Cas’ eyes slide away again. “I suppose. I just… I can’t be useful to you like this. I’m a burden.”

Dean shakes his head, frowning. “Hey, c’mon. You don’t have to be  _ useful,  _ dude. You’re family, it’s enough that you’re here and that you’re gonna be okay. This isn’t any different from that time Sam got hit with that gibberish curse or when I pulled my hamstring. How useful were either of us then, huh?”

Cas smirks grudgingly. “Not at all. You in particular. I had no idea that one person could possibly complain that much.” He tilts his head, remembering. “And you were very demanding.”

“Well  _ I’m _ sorry, I guess I coulda just let that vamp go to town on you. That what you woulda preferred?”

Cas huffs a weak laugh and Dean grins, taking in the way the furrow has more or less smoothed itself out of Cas’ miniature forehead. He feels his cheeks heat a little and he picks at a sliver of wood that’s working its way loose from the table. “Don’t… don’t ever think that the only reason we want you around is ‘cause you’re stupid powerful and handy in a tight spot. We like you, Cas, and that’s not gonna change whether you’re a human, an angel, or a limited edition action figure. Okay?”

Cas walks over the tabletop towards Dean and rests a hand on his arm. “Alright. I will try to remember that.”

Dean clears his throat. “So hey, you, uh… you wanna go watch something on TV?”

Cas smiles up at him. “There was a documentary that recently came out on Netflix that I’ve been meaning to watch.”

Dean groans. “Please tell me it’s not the bee one.”

Cas just smiles even wider. With a long-suffering sigh, Dean helps his weirdo nerd of a best friend onto his shoulder and gets up. “Fine. But afterwards we’re watching Tombstone.”

One of Cas’ tiny hands closes over Dean’s collar. “Only if you promise to wait at least a month after this before making me watch it again.”

“Oh, shut up.”

  
— - —

Leaning back for a wide angle, Sam snaps another picture, grinning hugely. Oh man. This is gonna be a _great_ addition to his blackmail stash. 

On the practical side, the spell wore off earlier than they’d expected, which is good. Sam’ll have to log it and call Rowena to ask why, but they might be able to get some useful information on faerie magic out of it. That’s always a plus, because faeries are slippery bastards who hate revealing their secrets. 

On the impractical side, though… Sam is going to get a  _ lot _ of enjoyment out of torturing Dean for the next few weeks. After all, it’s not every morning that you get to find your aggressively masculine older brother being tenderly spooned by an angel of the Lord on a couch that would struggle to comfortably fit one normal sized person, let alone two broad, muscular, six-foot-tall dudes. Even if those two dudes are pressed as closely together as Dean and Cas are.

Just wait ‘til Charlie hears about this, Sam thinks gleefully. She’s gonna  _ freak. _

Then he hits play on “Can’t Fight This Feeling”, and watches Dean blearily go through all five stages of grief in roughly ten seconds. 

Then Cas’ head pops up from behind Dean’s shoulder. “Good morning, Sam.” He yawns, his arm still curled over Dean’s waist, and blinks owlishly at the phone pointed towards them. “Can you send me those pictures?”

“That’s it—” Dean growls as he launches himself off the couch, and Sam’s delighted cackling echoes through the Bunker as he runs for his life.

**Notes for the Chapter:**

> This was so much fun to write. I love Sam so much, and maintain that he is a massive Destiel shipper, along with Charlie and basically everyone else who spends any amount of time with Cas and Dean. Honestly, the amount of UST is _criminal _.__


	5. Blackmail

**Notes for the Chapter:**

> One evening, a portal from hell opens up at the foot of your bed. A demon strides through, rips off your covers, and begins to drag you through the portal by your ankles. "You're going to help me settle a debt."
> 
> (Requested by wanzamaximoff)

Dean’s awake almost before the blankets have finished being ripped off him, pointing the gun he keeps under his pillow towards the shadowy figure at the bottom of the bed.

“What the—  _ Crowley?” _

The demon drops Dean’s blankets on the floor. “The one and only. Get up, Squirrel, we have places to be.” 

Sam’s awake by now, his gun joining Dean’s. “He’s not going anywhere,” he growls, standing up to move to Dean’s side.

Crowley raises his hands placatingly. “Stand down, Moose, I’m not here to kill you. No, I’m here on business.” He nods at Dean.  _ “You,  _ my trigger-happy friend, are going to help me settle a debt.” 

“No I’m not. I’m gonna give you five seconds to get outta here, and if you can’t manage that, I’m gonna shoot you. And then I’m gonna go back to sleep.” 

Crowley turns his eyes to the heavens, sighing loudly. “Satan help me. Do I have to spell everything out for you dolts?” He grits his teeth. “When I say settle a debt, I mean kill the snot-nosed bastard trying to collect. Normally I wouldn’t stoop to asking for your assistance, but the little twit’s pulled out some nasty tricks that I can’t overcome alone.” 

“Aw, poor you. Now fuck off,” Dean says, jerking his gun towards the door.

Crowley looks offended. “After everything I’ve done for you two idiots, you can’t even help me kill another demon? That’s what you  _ do! _ I’m practically handing him over on a silver platter!”

“Yeah, well,” Sam says. “We’re not interested. You’re barely an ally, Crowley, and you’re definitely not a friend.”

Crowley’s shoulders slump slightly as he looks between Sam and Dean. But then his gaze lands on Dean, and slowly, a smirk grows on his face. “You know... I’d hoped it wouldn’t come to this. Really, I did. But if you refuse to assist me, then I’m afraid I’ll be forced to tell sweet, innocent little Samuel here  _ exactly  _ what we got up to at the Black Spur before he showed up and crashed the party. You certainly… let  _ loose, _ didn’t you, Dean? Really explored all your options. I’m sure you remember.”

Dean goes pale, and then bright red. He doesn’t say anything. Sam looks at him warily, utterly confused. “Uh… Dean? What’s he talking about?”

Dean presses his lips together, grudgingly lowering his gun. He’s still flushed bright red. “Nothing.” He gets up, shoving his gun into the waistband of his jeans. “Fine. I’ll help you.” Crowley grins smugly, but Dean cuts him off. “Sam’s coming with, though. You get both of us, or neither.”

Sam makes a face, but follows Dean’s example and reluctantly puts his gun away. Crowley scowls. “Oh, fine, you bloody codependent children. I suppose two hulking flannel grunts is better than one.”

He stalks out of the motel room, and Sam looks over at Dean again. “Was he talking about when you were a demon? You told me you just bummed around that bar for, like, three weeks.”

Dean shrugs on a jacket. “Yeah. I did.” And without another word he follows Crowley outside.

Sam puzzles over it as he changes into some jeans and a shirt, wondering what Crowley could’ve been talking about.

Then a truly horrible thought strikes him halfway through doing up his boots. What if… no. No way. Dean and  _ Crowley? _

He shudders.

Nevermind. There are some things he just…  _ really  _ doesn’t need to know.

Well. Off to kill a demon it is.

**Notes for the Chapter:**

> I read this prompt, and immediately thought of this in relation to Dean’s time as a demon: “We did _extraordinary_ things to triplets.”
> 
> Interesting, Crowley. Verrrry interesting. 😏😂


	6. He’s My Cherry Pie

**Summary for the Chapter:**

> Castiel sans trench coat, plus “Cherry Pie” by Warrant, makes for one hell of a weird night.

**Notes for the Chapter:**

> Y’know the fandom joke that Cas without his trench coat is basically naked? Yeah. This comes from that, because that shit is _hilarious._
> 
> (Fear not, though, sweet readers: I do solemnly swear on on my car that Cas does not actually show up naked, or covered in bees. T rating still stands.)

Dean lounges in a chair at the map table, the book he’d been skimming for some last-minute research pushed aside as he finishes his whisky. It’s late; he’s gonna hit the sack after this, get some shut-eye. But for now it’s just him, his drink, and the classic rock mix he’s got playing softly on the fancy little Bluetooth speaker Sam got him for his birthday. 

“Since I’ve Been Loving You” peters off into silence, and Dean smiles as the chanting and the riff at the beginning of “Cherry Pie” comes on. Good song. It’s been stuck in his head all day, actually. 

He’s halfway through a drink when he sees movement out of the corner of his eye: it’s Cas, walking towards him through the library. He’s lost his trench coat, leaving him just in his black accountant suit. He looks strangely naked without it. 

Good, though. He looks good. 

Cas stops in the archway between the map room and the library, smiling faintly. With the library lights behind him turned down low for nighttime, it looks almost like he’s on stage or somethin’. He tilts his head. “Hello, Dean.”

Dean raises an eyebrow as he smiles back. “Evenin’, Cas. What’s up?”

Cas shakes his head, taking the last few steps down the stairs. “Nothing in particular. I just heard the music and realized you were still up.” Then Cas shrugs off his suit jacket and tosses it over the back of the chair at the head of the map table. Like it’s no biggie. Dean chokes on his reply, trying not to stare. He’s pretty sure he fails. 

But Cas isn’t done. He loosens his tie and pops the top few buttons of his shirt, then efficiently rolls up his sleeves before sitting down and angling himself towards Dean, that same soft, secretive smile still on his stupid, gorgeous fucking face. 

Dean’s still reeling from the rush of  _ holy fucking collarbones, Batman  _ and  _ forearms, shit, forearms  _ when Cas starts talking again. “What song is this?”

Dean clears his throat and takes a fortifying gulp of whisky. “Uh, Cherry Pie. By Warrant.” (Stop looking at his  _ hands, _ you  _ idiot,  _ that’s not making this any better—)

“Ah, yes. That’s the one with all the sexual innuendos, isn’t it?” Cas says mildly as he plucks Dean’s glass from his limp hand, downing the last swallow of whisky in one go. And Dean can’t even bring himself to be mad about it, not when he gets to watch the graceful line of Cas’ throat while he drinks. 

“Uh… yeah. That’s, um. Most rock, though.”

Cas puts the glass back down, meeting Dean’s eyes again. Dean shifts uncomfortably. “Are you… alright? You’re acting a little weird, man.”

Cas just smiles. “I’m fine, Dean. I’m wonderful.”

“Oh,” Dean says (squeaks) as Cas gets to his feet and stalks towards him. “Good.”

Cas stops in front of him, smiling rakishly. “Aren’t you going to ask me why?”

_ “Cool drink of water, such a sweet surprise,”  _ Jani Lane crows in the background. 

Dean swallows. “Um. Sure. What’s, uh, what’s got you so happy, Cas?”

Cas leans forward, planting his hands on the arms of Dean’s chair. Fuck, Dean’s going to  _ combust. _ “I realized something. Do you know what I realized?”

Dean manages a single shake of his head, his eyes sliding helplessly to Cas’ lips. His hands come up to rest on Cas’ hips, and the angel answers his own question. “I realized that you want me just as much as I want you, Dean.” 

He lets out a sharp breath. “Fuck, Cas, I…”

Cas smiles. “I know.” 

_ “Sweet, cherry pie…” _

And then Cas is closing the distance between them, fucking  _ finally,  _ his legs bumping against the insides of Dean’s thighs as he sidles forward. There’s barely a breath left between them, Dean swears he’s about to either ascend or pass out, and—

He bolts upright in bed, heart racing, gasping for breath. His face is on  _ fire _ .

Which is kind of impressive, actually, because he’s also maintaining a raging hard-on at the same time.

Dean flops back onto his pillows, throwing one arm over his eyes and studiously attempting to ignore the situation in his boxers. Whatever happened to  _ normal _ stripper dreams? Because fucking  _ christ,  _ that was  _ totally  _ a stripper dream. He used to get a nice, uncomplicated chick based off of whoever his last lay was. But no more. No,  _ now _ he gets Cas. Who is somehow leaps and bounds hotter than any of those dream girls ever were.

“Fuck,” he says aloud, to no one in particular. 

He has  _ got  _ to stop listening to Warrant before bed.

**Notes for the Chapter:**

> So yeah, “Cherry Pie” by Warrant is a banger and you should all go listen. And on that topic, so is “Night Moves” by our man Bob Seger. I just watched 11x04 for the first time yesterday, so that’s been running through my head ALL DAY.
> 
> Hope y’all liked this one! Drop prompts you’d like to see in the comments, I’m always open to inspiration. :)


End file.
